JPH0645603B2 - 光学活性２‐オキソイミダゾリジン誘導体の製法 - Google Patents

光学活性２‐オキソイミダゾリジン誘導体の製法

Info

Publication number: JPH0645603B2
Authority: JP; Japan
Prior art keywords: oxoimidazolidine; configuration; group; derivative; compound
Prior art date: 1988-12-16
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

JP63318745A

Other languages

English (en)

Japanese (ja)

Other versions

JPH02164869A (ja

Inventor

公明林

均窪田

Original Assignee

田辺製薬株式会社

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1988-12-16

Filing date

1988-12-16

Publication date

1994-06-15

1988-12-16 Application filed by 田辺製薬株式会社 filed Critical 田辺製薬株式会社

1988-12-16 Priority to JP63318745A priority Critical patent/JPH0645603B2/ja

1989-11-27 Priority to IL92456A priority patent/IL92456A0/xx

1989-12-04 Priority to US07/445,060 priority patent/US5013845A/en

1989-12-04 Priority to FI895795A priority patent/FI97133C/fi

1989-12-05 Priority to CN89109175A priority patent/CN1032308C/zh

1989-12-05 Priority to CA002004606A priority patent/CA2004606C/en

1989-12-12 Priority to ES89312965T priority patent/ES2062044T3/es

1989-12-12 Priority to AT89312965T priority patent/ATE100817T1/de

1989-12-12 Priority to EP89312965A priority patent/EP0373881B1/de

1989-12-12 Priority to AU46195/89A priority patent/AU622959B2/en

1989-12-12 Priority to DE89312965T priority patent/DE68912745T2/de

1989-12-14 Priority to IE400489A priority patent/IE64315B1/en

1989-12-15 Priority to KR1019890018658A priority patent/KR950009364B1/ko

1989-12-15 Priority to HU896640A priority patent/HU203730B/hu

1989-12-15 Priority to DK198906382A priority patent/DK174701B1/da

1990-06-25 Publication of JPH02164869A publication Critical patent/JPH02164869A/ja

1994-06-15 Publication of JPH0645603B2 publication Critical patent/JPH0645603B2/ja

1995-01-13 Priority to SG4795A priority patent/SG4795G/en

1995-03-09 Priority to HK34195A priority patent/HK34195A/en

2009-06-15 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical class O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 title claims abstract description 9
238000000034 method Methods 0.000 title abstract description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims abstract description 10
125000003118 aryl group Chemical group 0.000 claims abstract description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
238000004519 manufacturing process Methods 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 23
-1 propionic acid compound Chemical class 0.000 claims description 16
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 8
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
235000019260 propionic acid Nutrition 0.000 claims description 4
150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
239000000047 product Substances 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 12
239000002904 solvent Substances 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
238000010898 silica gel chromatography Methods 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
238000001816 cooling Methods 0.000 description 6
238000001914 filtration Methods 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
229930182843 D-Lactic acid Natural products 0.000 description 5
JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
229940022769 d- lactic acid Drugs 0.000 description 5
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 5
238000003756 stirring Methods 0.000 description 5
239000006188 syrup Substances 0.000 description 5
235000020357 syrup Nutrition 0.000 description 5
UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 4
108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
238000006482 condensation reaction Methods 0.000 description 4
239000012043 crude product Substances 0.000 description 4
239000013078 crystal Substances 0.000 description 4
150000002148 esters Chemical group 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000010531 catalytic reduction reaction Methods 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000011259 mixed solution Substances 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
WORJRXHJTUTINR-UHFFFAOYSA-N 1,4-dioxane;hydron;chloride Chemical compound Cl.C1COCCO1 WORJRXHJTUTINR-UHFFFAOYSA-N 0.000 description 2
KZKRPYCBSZIQKN-UHFFFAOYSA-N 2-Imidazolidone-4-carboxylic acid Chemical class OC(=O)C1CNC(=O)N1 KZKRPYCBSZIQKN-UHFFFAOYSA-N 0.000 description 2
OZGMODDEIHYPRY-UHFFFAOYSA-N 2-bromopropanoyl chloride Chemical compound CC(Br)C(Cl)=O OZGMODDEIHYPRY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
VYEIIPLQOBKTAZ-INIZCTEOSA-N benzyl (2s)-2-amino-4-phenylbutanoate Chemical compound C([C@H](N)C(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 VYEIIPLQOBKTAZ-INIZCTEOSA-N 0.000 description 2
SXTMXSXWPZPIFG-JTQLQIEISA-N benzyl (4s)-1-methyl-2-oxoimidazolidine-4-carboxylate Chemical compound N1C(=O)N(C)C[C@H]1C(=O)OCC1=CC=CC=C1 SXTMXSXWPZPIFG-JTQLQIEISA-N 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
WFLQXECQLHZKMV-NSHDSACASA-N ethyl (2s)-2-amino-4-phenylbutanoate Chemical compound CCOC(=O)[C@@H](N)CCC1=CC=CC=C1 WFLQXECQLHZKMV-NSHDSACASA-N 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
125000005948 methanesulfonyloxy group Chemical group 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
230000006340 racemization Effects 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
QXYOROBKCZWFKK-MRVPVSSYSA-N (2r)-2-(4-methylphenyl)sulfonyloxypropanoic acid Chemical compound OC(=O)[C@@H](C)OS(=O)(=O)C1=CC=C(C)C=C1 QXYOROBKCZWFKK-MRVPVSSYSA-N 0.000 description 1
LFMBKSRGQHUJKP-GSVOUGTGSA-N (2r)-2-methylsulfonyloxypropanoic acid Chemical compound OC(=O)[C@@H](C)OS(C)(=O)=O LFMBKSRGQHUJKP-GSVOUGTGSA-N 0.000 description 1
AEDVCQIVTIIFMO-VKHMYHEASA-N (4s)-1-methyl-2-oxoimidazolidine-4-carboxylic acid Chemical compound CN1C[C@@H](C(O)=O)NC1=O AEDVCQIVTIIFMO-VKHMYHEASA-N 0.000 description 1
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
CLLUGLDDQWJYGB-RNCAPKPVSA-N benzyl (4s)-1-methyl-2-oxo-3-[(2s)-2-[[(2s)-1-oxo-4-phenyl-1-phenylmethoxybutan-2-yl]amino]propanoyl]imidazolidine-4-carboxylate Chemical compound C([C@H](N[C@@H](C)C(=O)N1C(N(C)C[C@H]1C(=O)OCC=1C=CC=CC=1)=O)C(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 CLLUGLDDQWJYGB-RNCAPKPVSA-N 0.000 description 1
CCERYCGXHHHRHJ-VJBMBRPKSA-N benzyl (4s)-3-[(2s)-2-[[(2s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-1-methyl-2-oxoimidazolidine-4-carboxylate Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1C(N(C)C[C@H]1C(=O)OCC=1C=CC=CC=1)=O)CC1=CC=CC=C1 CCERYCGXHHHRHJ-VJBMBRPKSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
PTFKZMFFSIYCOV-MERQFXBCSA-N ethyl (2s)-2-amino-4-phenylbutanoate;hydrochloride Chemical compound Cl.CCOC(=O)[C@@H](N)CCC1=CC=CC=C1 PTFKZMFFSIYCOV-MERQFXBCSA-N 0.000 description 1
WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
KLZWOWYOHUKJIG-BPUTZDHNSA-N imidapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1C(N(C)C[C@H]1C(O)=O)=O)CC1=CC=CC=C1 KLZWOWYOHUKJIG-BPUTZDHNSA-N 0.000 description 1
VFAVNRVDTAPBNR-UBHSHLNASA-N imidaprilat Chemical compound C([C@H](N[C@@H](C)C(=O)N1C(N(C)C[C@H]1C(O)=O)=O)C(O)=O)CC1=CC=CC=C1 VFAVNRVDTAPBNR-UBHSHLNASA-N 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
IJHISIJZHFRRSM-UHFFFAOYSA-M sodium;2-methylpropan-2-ol;hydroxide Chemical compound [OH-].[Na+].CC(C)(C)O IJHISIJZHFRRSM-UHFFFAOYSA-M 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/022—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2
- C07K5/0222—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2 with the first amino acid being heterocyclic, e.g. Pro, Trp
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- C07D233/38—One oxygen atom with acyl radicals or hetero atoms directly attached to ring nitrogen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Biochemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Molecular Biology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Biophysics (AREA)
Genetics & Genomics (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP63318745A 1988-12-16 1988-12-16 光学活性２‐オキソイミダゾリジン誘導体の製法 Expired - Lifetime JPH0645603B2 (ja)

Priority Applications (17)

Application Number	Priority Date	Filing Date	Title
JP63318745A JPH0645603B2 (ja)	1988-12-16	1988-12-16	光学活性２‐オキソイミダゾリジン誘導体の製法
IL92456A IL92456A0 (en)	1988-12-16	1989-11-27	Preparation of optically active 2-oxoimidazolidine derivatives
US07/445,060 US5013845A (en)	1988-12-16	1989-12-04	Process for preparing optically active 2-oxoimidazolidine derivatives
FI895795A FI97133C (fi)	1988-12-16	1989-12-04	Menetelmä optisesti aktiivisten 2-oksoimidatsolidiinijohdannaisten valmistamiseksi
CN89109175A CN1032308C (zh)	1988-12-16	1989-12-05	制备旋光性2-氧代咪唑烷衍生物的方法
CA002004606A CA2004606C (en)	1988-12-16	1989-12-05	Process for preparing optically active 2-oxoimidazolidine derivatives
AU46195/89A AU622959B2 (en)	1988-12-16	1989-12-12	Process for preparing optically active 2-oxoimidazolidine derivatives
AT89312965T ATE100817T1 (de)	1988-12-16	1989-12-12	Herstellung von optisch aktiven 2-oxoimidazolidin-derivaten.
EP89312965A EP0373881B1 (de)	1988-12-16	1989-12-12	Herstellung von optisch aktiven 2-Oxoimidazolidin-derivaten
ES89312965T ES2062044T3 (es)	1988-12-16	1989-12-12	Un procedimiento para preparar un derivado de 2-oxoimidazolidina opticamente activo.
DE89312965T DE68912745T2 (de)	1988-12-16	1989-12-12	Herstellung von optisch aktiven 2-Oxoimidazolidin-derivaten.
IE400489A IE64315B1 (en)	1988-12-16	1989-12-14	Process for preparing optically active 2-oxoimidaTzolidine derivatives T
HU896640A HU203730B (en)	1988-12-16	1989-12-15	Process for producing optically active 2-oxo-imidazolidine derivatives
KR1019890018658A KR950009364B1 (ko)	1988-12-16	1989-12-15	광학 활성 2-옥소이미다졸리딘 유도체의 제조 방법
DK198906382A DK174701B1 (da)	1988-12-16	1989-12-15	Fremgangsmåde til fremstilling af optisk aktive 2-oxoimidazolidinderivater og 3-acyl-2-oxoimidazolidinmellemprodukt
SG4795A SG4795G (en)	1988-12-16	1995-01-13	Process for preparing optically active 2-oxoimidazzolidine derivatives
HK34195A HK34195A (en)	1988-12-16	1995-03-09	Process for preparing optically active 2-oxoimidazolidine derivatives

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP63318745A JPH0645603B2 (ja)	1988-12-16	1988-12-16	光学活性２‐オキソイミダゾリジン誘導体の製法

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
JP5309565A Division JPH07121916B2 (ja)	1993-12-10	1993-12-10	光学活性３−アシル−２−オキソイミダゾリジン−４−カルボン酸誘導体及びその製法

Publications (2)

Publication Number	Publication Date
JPH02164869A JPH02164869A (ja)	1990-06-25
JPH0645603B2 true JPH0645603B2 (ja)	1994-06-15

Family

ID=18102470

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP63318745A Expired - Lifetime JPH0645603B2 (ja)	1988-12-16	1988-12-16	光学活性２‐オキソイミダゾリジン誘導体の製法

Country Status (17)

Country	Link
US (1)	US5013845A (de)
EP (1)	EP0373881B1 (de)
JP (1)	JPH0645603B2 (de)
KR (1)	KR950009364B1 (de)
CN (1)	CN1032308C (de)
AT (1)	ATE100817T1 (de)
AU (1)	AU622959B2 (de)
CA (1)	CA2004606C (de)
DE (1)	DE68912745T2 (de)
DK (1)	DK174701B1 (de)
ES (1)	ES2062044T3 (de)
FI (1)	FI97133C (de)
HK (1)	HK34195A (de)
HU (1)	HU203730B (de)
IE (1)	IE64315B1 (de)
IL (1)	IL92456A0 (de)
SG (1)	SG4795G (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN104513292A (zh) *	2013-09-29	2015-04-15	山东新时代药业有限公司	一种雷米普利的制备方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5788165A (en) *	1980-11-21	1982-06-01	Tanabe Seiyaku Co Ltd	2-oxoimidazolidine-4-carboxylic acid derivative and its preparation
JPS6058233B2 (ja) *	1982-05-24	1985-12-19	田辺製薬株式会社	２−オキソイミダゾリジン誘導体及びその製法
JPS6058233A (ja) *	1983-08-11	1985-04-04	ザ・アプジヨン・カンパニー	滅菌懸濁液及び溶液の保持及び混合装置

1988
- 1988-12-16 JP JP63318745A patent/JPH0645603B2/ja not_active Expired - Lifetime
1989
- 1989-11-27 IL IL92456A patent/IL92456A0/xx unknown
- 1989-12-04 FI FI895795A patent/FI97133C/fi active IP Right Grant
- 1989-12-04 US US07/445,060 patent/US5013845A/en not_active Expired - Lifetime
- 1989-12-05 CN CN89109175A patent/CN1032308C/zh not_active Expired - Lifetime
- 1989-12-05 CA CA002004606A patent/CA2004606C/en not_active Expired - Lifetime
- 1989-12-12 AT AT89312965T patent/ATE100817T1/de not_active IP Right Cessation
- 1989-12-12 DE DE89312965T patent/DE68912745T2/de not_active Expired - Lifetime
- 1989-12-12 AU AU46195/89A patent/AU622959B2/en not_active Expired
- 1989-12-12 EP EP89312965A patent/EP0373881B1/de not_active Expired - Lifetime
- 1989-12-12 ES ES89312965T patent/ES2062044T3/es not_active Expired - Lifetime
- 1989-12-14 IE IE400489A patent/IE64315B1/en not_active IP Right Cessation
- 1989-12-15 DK DK198906382A patent/DK174701B1/da not_active IP Right Cessation
- 1989-12-15 KR KR1019890018658A patent/KR950009364B1/ko not_active Expired - Lifetime
- 1989-12-15 HU HU896640A patent/HU203730B/hu unknown
1995
- 1995-01-13 SG SG4795A patent/SG4795G/en unknown
- 1995-03-09 HK HK34195A patent/HK34195A/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
HK34195A (en)	1995-03-17
US5013845A (en)	1991-05-07
HU896640D0 (en)	1990-02-28
EP0373881A3 (en)	1990-08-16
DK638289D0 (da)	1989-12-15
DK174701B1 (da)	2003-09-29
EP0373881B1 (de)	1994-01-26
CA2004606A1 (en)	1990-06-16
AU4619589A (en)	1990-06-21
IE64315B1 (en)	1995-07-26
CN1043705A (zh)	1990-07-11
KR950009364B1 (ko)	1995-08-21
ATE100817T1 (de)	1994-02-15
FI97133B (fi)	1996-07-15
IE894004L (en)	1990-06-16
SG4795G (en)	1995-06-16
CA2004606C (en)	1997-01-07
HUT52064A (en)	1990-06-28
HU203730B (en)	1991-09-30
CN1032308C (zh)	1996-07-17
FI895795A0 (fi)	1989-12-04
DK638289A (da)	1990-06-17
AU622959B2 (en)	1992-04-30
EP0373881A2 (de)	1990-06-20
DE68912745D1 (de)	1994-03-10
JPH02164869A (ja)	1990-06-25
ES2062044T3 (es)	1994-12-16
IL92456A0 (en)	1990-08-31
DE68912745T2 (de)	1994-05-11
FI97133C (fi)	1996-10-25
KR900009603A (ko)	1990-07-05

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Publication	Publication Date	Title
FR2620699A1 (fr)	1989-03-24	Procede de synthese d'alpha amino acides n alkyles et de leurs esters. application a la synthese de carboxyalkyl dipeptides
JPH02191251A (ja)	1990-07-27	（２Ｓ，３↓ａＳ，７↓ａＳ）−２−カルボキシペルヒドロインドールの工業的合成法
KR100520700B1 (ko)	2005-10-17	Ｎ-[(ｓ)-1-카르복시부틸]-(ｓ)-알라닌 에스테르의 합성방법 및 페린도프릴 합성에서의 용도
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EP0635002B1 (de)	1998-07-22	Neue perhydroisoindolderivate und ihre herstellung
EP1354876B1 (de)	2005-04-27	Verfahren zur Synthese von (2S,3aS,7aS)-Perhydroindol-2-carbonsäure und seiner Estern, und Verwendung in der Synthese von Perindopril
KR101233983B1 (ko)	2013-02-18	페린도프릴의 제조방법
JPH0645603B2 (ja)	1994-06-15	光学活性２‐オキソイミダゾリジン誘導体の製法
CA1274347A (fr)	1990-09-18	Derives d'acides isoindoledicarboxyliques et leur procede de preparation
WO2004083237A1 (fr)	2004-09-30	NOUVEAU PROCEDE DE SYNTHESE DE L’ACIDE (2S, 3aS, 7aS)-PERHYDROINDOLE-2-CARBOXYLIQUE ET DE SES ESTERS, ET APPLICATION A LA SYNTHESE DU PERINDOPRIL
WO2005023842A1 (fr)	2005-03-17	Nouveau procede de synthese du perindopril et de ses sels pharmaceutiquement acceptables
JPH07121916B2 (ja)	1995-12-25	光学活性３−アシル−２−オキソイミダゾリジン−４−カルボン酸誘導体及びその製法